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  • 1
    Electronic Resource
    Electronic Resource
    The cationic polymerization of 2-alkenylfurans, 2Part 1: cf.5. A side reaction leading to polyunsaturated products (1982)
    New York : Wiley-Blackwell
    Die Makromolekulare Chemie 183 (1982), S. 2399-2413 
    Details
    ISSN: 0025-116X
    Keywords: Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology , Physics
    Notes: A spectroscopic and conductimetric study of the cationic polymerization of 2-vinylfuran (1) and 2-methyl-5-venylfuran (2) showed the existence of an important side reaction originating from a hydride-ion shift from an unsaturated polymer molecule to an active species. The resulting allylic carbocation, in equilibrium with a doubly unsaturated polymer molecule, can react further and the repetition of the mechanism on progressively more conjugated species leads to the formation of a series of highly charge-delocalized carbenium ions absorbing throughout the visible region of the spectrum (and giving high electrical conductivity) and of neutral polyconjugated polymer molecules. Since the hydride-ion abstraction occurs from the tertiary carbon atom of the vinylic chain, vinylidene polymers of monomers such as 2-isopropenylfuran (3) and 2-isopropenyl-5-methylfuran (4) are not susceptible to it. Indeed, their cationic polymerization proceeds without colour formation and conductivity increase.
    Additional Material: 7 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/macp.1982.021831010
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  • 2
    Electronic Resource
    Electronic Resource
    Vinylkationen, 36. Solvolyse von Cycloalkylidenmethyl- und 1-Cyclopenten-1-yl-triflaten (1982)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 115 (1982), S. 772-782 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Vinyl Cations, 36. Solvolysis of Cycloalkylidenemethyl and 1-Cyclopenten-1-yl TriflatesCyclohexlidenemethyl triflate (2), cyclobutylidenemethyl triflate (5), 1-cyclopenten-1-yl triflate (7), bicyclo [3.1.0]hex-2-en-2-yl triflate (9), 1-cyclobutylideneethyl triflate (19), and 2-methyl-1-cyclopenten-1-yl triflate (29) were solvolyzed in solvents of various ionizing power and nucleophilicity and the solvolysis products were identified. The cyclobutylidenealkyl triflates solvolyze via a vinyl cation mechanism involving ion pairs with rearrangement to cyclopentene and cyclopentanone compounds. The 1-cyclopenten-1-yl triflates do not produce vinyl cation intermediates but give only the corresponding ketones via an O—S bond cleavage of the triflate group.
    Notes: Cyclohexylidenmethyl-triflat (2), Cyclobutylidenmethyl-triflat (5), 1-Cyclopenten-1-yl-triflat (7), Bicyclo[3.1.0]hex-2-en-2-yl-triflat (9), 1-Cyclobutylidenethyl-triflat (19) und 2-Methyl-1-cyclopenten-1-yl-triflat (29) wurden in Lösungsmitteln verschiedener Ionisierungsstärke und Nucleophilie solvolysiert und die Solvolyseprodukte aufgeklärt. Die Cyclobutylidenalkyl-triflate solvolysieren über Ionenpaarmechanismen (Vinylkationen) unter Umlagerung zu Cyclopenten- und Cyclopentanon-Derivaten. Die 1-Cyclopenten-1-yl-triflate reagieren nicht über Vinylkationen als Zwischenstufe, sondern unter O—S-Spaltung zu den entsprechenden Ketonen.
    Additional Material: 6 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19821150238
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  • 3
    Electronic Resource
    Electronic Resource
    The mechanism of O3-aldehyde reactions (1982)
    New York, NY : Wiley-Blackwell
    International Journal of Chemical Kinetics 14 (1982), S. 237-249 
    Details
    ISSN: 0538-8066
    Keywords: Chemistry ; Physical Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: A new mechanism is proposed for gas-phase O3-aldehyde reactions. Certain aspects of the new mechanism may be applicable also to O3-aldehyde reactions in solution. The proposed mechanism involves initiation by addition of O3 across the aldehydic C=O bond. The initiation process and the subsequent chemistry together represent an exact analogue of the Criegee mechanism for O3-alkene reactions.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/kin.550140304
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  • 4
    Electronic Resource
    Electronic Resource
    Kinetics and energetics of the criegee intermediate in the gas phase. II. The criegee intermediate in the photooxidation of formaldehyde, in alkyldioxy disproportionation and O + oxoalkane addition reactions (1982)
    New York, NY : Wiley-Blackwell
    International Journal of Chemical Kinetics 14 (1982), S. 225-236 
    Details
    ISSN: 0538-8066
    Keywords: Chemistry ; Physical Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The gas-phase kinetics and energetics of the Criegee intermediate, deduced from studies of O3-alkene systems, suggest that a hydroxy-substituted Criegee intermediate probably participates in the photooxidation of formaldehyde. In contradistinction, the existing evidence suggests that the Criegee intermediate and its isomers are probably not involved in alkyldioxy disproportionation reactions. In the case of O + oxoalkane addition reactions, the Criegee intermediate and its isomers are discussed in terms of a complex equilibrium: .
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/kin.550140303
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  • 5
    Electronic Resource
    Electronic Resource
    Cyclobutane production via the O3--thiolane reaction (1982)
    New York, NY : Wiley-Blackwell
    International Journal of Chemical Kinetics 14 (1982), S. 439-445 
    Details
    ISSN: 0538-8066
    Keywords: Chemistry ; Physical Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/kin.550140410
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  • 6
    Electronic Resource
    Electronic Resource
    Influence of enol acetylation on the photo-fries rearrangement of an ortho-acylaryl benzoate (1982)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1982 (1982), S. 2238-2243 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Einfluß der Enol-Acetylierung auf die Photo-Fries-Umlagerung eines Benzoesäure-ortho-acylarylestersDas Enolacetat 1b erleidet bei Bestrahlung Spaltung der Benzoyl-Sauerstoff-Bindung, wobei eine Mischung der Benzophenone 4 und 5 resultiert. Die primär entstehenden Photo-Fries-Produkte 2 und 3 konnten infolge einer schnellen intramolekularen Umacetylierung nicht isoliert werden. Das Acetophenon 6 lagert sich unter den gleichen experimentellen Bedingungen zu den Benzophenonen 7 und 8 um, jedoch sind die Ausbeuten bemerkenswert niedriger als im obigen Fall. Die Verbindungen 7 und 8 werden durch Acetanhydrid in Gegenwart von Pyridin in die jeweiligen Essigsäureester 4 und 5 übergeführt.
    Notes: The enol acetate 1b undergoes benzoyl-oxygen bond rupture upon irradiation, giving a mixture of benzophenones 4 and 5. The primary photo-Fries products 2 and 3 could not be isolated, due to a rapid intramolecular transacetylation. The acetophenone 6 rearranges to give the benzophenones 7 and 8 under the same conditions, but the yields are significantly lower than in the former case. Compounds 7 and 8 are separately correlated with 4 and 5 by treatment with acetic anhydride in the presence of pyridine.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198219821214
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  • 7
    Electronic Resource
    Electronic Resource
    Kinetics and energetics of the criegee intermediate in the gas phase. I. The criegee intermediate in ozone-alkene reactions (1982)
    New York, NY : Wiley-Blackwell
    International Journal of Chemical Kinetics 14 (1982), S. 201-224 
    Details
    ISSN: 0538-8066
    Keywords: Chemistry ; Physical Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The chemistry and energetics of the Criegee intermediate, a primary product of the ozonolysis of alkenes, are discussed in terms of recent ab-initio calculations and laboratory studies. The experimental observations in O3-alkene systems can be rationalized on the basis of a general mechanism: where the
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/kin.550140302
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